RJ Cutler spent an entire year with Wintour with the specific mission of capturing life at Vogue as they launch their most successful issue of the year – The September Issue. Unparalleled access to Wintour and her Vogue world included treks around the world with with the renowned editirix. Fresh from his world-wide whirlwind The September Issue shoot, sat down to chat about The September Issue and Anna Wintour.

First, I was curious what you took away from your time with Anna Wintour that can explain how this brilliant woman has remained powerfully relevant in a world that changes each season?

RJ Cutler: What struck me most was her management style. She has a decisiveness and her faith in her own instincts this is unmatched. At the same time, her clear awareness that surrounding herself with the highest level of talent she possibly could was a wise thing to do. So you have these two very strong impulses that when working together, I think, are very instructive, you know – in terms of leadership.

What did you take away in terms of her leadership toolbox?

RJ Cutler: She has a kind of…no looking back. She says in the movie, fashion’s not about looking back, it’s about looking forward. She loves the saying ‘onto the next’ which is a Karl Lagerfeld expression that she references a lot. On the other hand, as you see in the movie, she’s one of those leaders who aren’t afraid to have really strong minded, really talented people, around her – even people who don’t necessarily agree with her.

How did it come about that you had access to not only Anna Wintour working her magic, but as a filmmaker to capture the creative collective that is creating the September issue of Vogue? Were you surprised you were allowed this access?

RJ Cutler: No, not really. This is what I do, I’d say you always get it when you want it, but, Anna and I met and we started talking about working together. We agreed we’d do it. Maybe you don’t get surprised when you get access to the things that I’ve had access to…I don’t ever want to take it for granted. I’ve been very fortunate in the places I’ve been able to make films and the stories I’ve been able to tell. But, once I knew that Anna wanted to work with me on a project, I wasn’t surprised that would be the September issue.

For you going in, were there any expectations? If so, how did expectations play out versus what you experienced?

RJ Cutler: You touched on a key part of my process, which is to limit my expectations as much as possible. My most valuable resource is my curiosity. The more that I don’t have preconceived notions, the more successful I’m going to be because then curiosity leads to discovery. Discovery is what allows us to make the film. The more you operate out of your own expectations, the more you see things clearly.

For you as a filmmaker, I’m looking at all the different subjects you’ve covered and the mediums in which they’ve been seen. Is the process still a continuing education type of situation?
RJ Cutler: Oh, yes. You’re always, well, on one hand you’re always re-learning how to do it. But, more importantly, every subject is a new challenge and new discovery. When you finish the film you know all these things about the subject that you’ve made you’re film about. But, when you start the next film, you’re starting with a blank slate.

Is that one of the most enjoyable aspects of your work, learning new worlds?

RJ Cutler: It’s not only enjoyable, it’s a privilege. With each project you receive this invitation to float into somebody’s world and lives and their stories — then, to tell their stories. I get to see the world through their eyes for a rather lengthy period of time. I got to experience up-close Anna Wintour’s world, and what a privilege.

One of those worlds was the War Room. As a producer behind the War Room, it’s almost as if that film’s title has become part of the vernacular over the years to describe documentary filmmaking.
RJ Cutler: Thank you…

Being a part of that…I don’t know if you could even quantify the effect it’s had on how people view things.
RJ Cutler: It’s an interesting question. It’s certainly a benchmark. You look back on that movie and you see the direction the world was pointed in, in 1992 — especially the world of political campaigns and media, communication. But, you also you can see how dramatically the world has changed in a mere 17 years. When we were making The War Room, the whole thing about the Clinton campaign was that they were cutting edge communicators. They were going to show the Republicans that if the republicans took a swing at them, they would take a swing right back — and by right back they meant in the same news cycle. Now, those news cycles have been reduced to 30 seconds, a minute?

120-character news cycles is the world that we live in right now. It’s such a dramatic change. You look at War Room today – it looks like they were working in the Stone Age. But, that’s the beauty of these films. You capture a moment in time. You reflect back on that moment in time.

What first compelled you to make a life out of telling people’s stories?
RJ Cutler: I have to say, as early as first grade I was directing plays in the schoolyard and I was also running the school newspaper. Really, the combination of dramatic storytelling and storytelling about the real world is what I do in documentaries. I see these movies as movies. They’re dramatic narratives. I want the audience, when they come to see any of my films, and The September Issue is a perfect example, to have a great time at the movies. My goal is to have it be cinematic and engaging and dramatic and emotional – all the things that you think of when you go to the movies. Part of what is so exciting to me is that these stories are taking place in the real world.